This week, host Alex Bond sits down with Tanner Hackett, CEO of Counterpart, a management liability and professional liability MGA that has written 35,000 policies for small businesses and raised $106 million to take on the inefficiencies baked into traditional insurance.

Tanner's background isn't in insurance — it's in technology. He built and sold companies in e-commerce and marketing tech before turning his attention to this industry. That outsider perspective shapes everything about how Counterpart operates.

In this episode, they cover:

→ Why the insurance industry now has collective awareness of AI's importance — but awareness and action are very different things

→ How being built AI-first from inception gives Counterpart a different starting point to legacy carriers

→ The case for flatter organisational structures and why giving people more information and autonomy leads to better outcomes than traditional hierarchy

→ What's driving rising claims severity and frequency and how business pressures on small companies are feeding through into losses

→ Counterpart's expansion into financial institutions coverage, and the product-launch infrastructure they've built to move faster

Tanner also reflects on the unique challenge facing small businesses as AI becomes unavoidable and why he believes insurers should be doing more than just providing coverage.

Well worth your time, wherever you sit in the industry.

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What if the broker channel — often written off as too traditional, too slow, too analogue — is actually where AI's impact on insurance will be felt most?

Alex sits down with Martin F., co-founder of Foliume, to explore exactly that question in this week's episode.

Founded in 2022, Foliume is on a mission to reinvent insurance distribution by putting AI at the centre of how brokers and agencies work — reducing the administrative burden that consumes their days and giving them back time to do what they do best: build relationships, understand risk, and serve customers.

Martin breaks down Foliume's dual AI approach — assisted tools that keep brokers in control, and autonomous systems capable of handling customer interactions end-to-end across channels like WhatsApp — and explains why getting that balance right is everything.

The conversation covers:

🌍 Why Spain was the proving ground and why the UK is next

💰 Foliume's recent funding round with PitchDrive and Telefónica

🤖 Why AI is creating a genuine opening to challenge the legacy software houses that have long dominated the broker market

📈 The $3 trillion opportunity Sequoia identified — and what it means for insurance distribution

"InsurTech 1.0 was about distribution. This wave is about relationships."

A fascinating episode for anyone thinking about where AI, brokers, and the future of insurance distribution intersect.

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This week, host Alex Bond sits down with Will Ross, co-founder and CEO of Federato — the AI-native core platform transforming the full insurance policy lifecycle, from underwriting to claims and billing.

Will and his Stanford AI research co-founder built Federato on a simple but bold premise: AI should support high-value human decision-making, not just cut costs. And they're putting that conviction to the test.

In this episode, Alex and Will discuss:

🏗️ Why legacy "old core" insurance systems can't be fixed by bolting AI on top and what a genuinely AI-native alternative looks like

📈 The results that speak for themselves: one client saw a 2.2x increase in quote volume, an 89% reduction in time to quote, and improved high-appetite risk selection from 1 in 10 to 6 in 10, all within 90 days

💰 Why Federato raised $100 million in Series D funding from Goldman Sachs even though they didn't need the capital

🔄 How the conversation around AI in insurance has evolved from cost-cutting to genuinely transforming outcomes

🤝 Why Will believes in being radically honest with clients about the scale of change required and why that's built trust rather than lost it

This is a conversation about what it really takes to modernise insurance from the inside out and why incremental change isn't going to cut it.

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This week, host Dan Briselden sits down with Stephen Stonberg, CEO & co-founder of Tabit Insurance — a company bridging the world of Bitcoin and the balance sheet of a regulated insurer.

Stephen shares how Tabit is using centuries-old Lombard lending principles to do something genuinely new: bringing Bitcoin onto an insurance balance sheet — dollarising it, holding it securely, and opening up a fresh source of capital for an industry that's long relied on the same investor pool.

In this episode, you'll hear Stephen's take on:

• Why Barbados is a top-10 global captive domicile and why that matters for crypto
• The tax problem that stops Bitcoin holders from generating yield and how insurance solves it
• Why the insurance industry is the hardest audience to convince (harder than capital markets)
• How AI is already reshaping how Tabit thinks about distribution and staffing
• The new insurance lines that don't yet exist and who's going to build them

"The insurance industry needs new capital. Bitcoin holders need yield. It's not rocket science — you just need all the right ingredients." — Stephen Stonberg

Whether you're in reinsurance, capital markets or just watching the crypto-insurance space evolve, this is a conversation worth your time.

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In the latest episode, host Alex Bond sits down with Chris Luiz, the founder behind one of Insurtech's most community-driven conferences: the Scout InsurTech event in Columbus, Ohio, which has grown to over 80 startups and nearly 500 attendees this year.

What makes the Scout InsurTech conference different:

🚫 No expo floor, no paid mainstage slots, no junior salespeople filling seats

🤝 Structured networking designed to create real business interactions

🎯 Decision-makers only — the kind of room the bigger Vegas and New York events can't replicate

What else they cover:

• 💡 The real state of MGA innovation — where VC has pulled back and where opportunity still exists in parametric and embedded insurance
• 💰 Why a PE-style model might suit MGA builders better than traditional venture capital
• 🤖 How AI is levelling the playing field between large tech-forward carriers and mid-sized mutuals — and what that means for the next decade
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Whether you're building an MGA, thinking about where smart capital should go next, or simply want a front-row seat to where Insurtech is heading, this episode is a genuinely honest conversation from someone who has been at the heart of the community for years.

#LeadershipInInsurance #InsurTech #MGA #AI #Insurance #Podcast #ScoutInsurTech

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This week, host Alex Bond sits down with James Thom, Chief Product Officer at Vertafore, the insurance technology company powering agencies, MGAs, and carriers across the US and Canada.

James brings a fascinating perspective: from consulting at McKinsey to leading product at scale, he's seen first-hand why making the leap from recommendation to real-world implementation changes everything.

In this episode, we get into:

💡 Why AI transformation requires more than piecemeal adoption — and why the companies going all-in are seeing 2x–3x productivity gains

🏗️ How Vertafore's new Velocity AI platform is embedding AI natively into the tools insurers already use every day

🔄 The "human plus" moment — giving every individual a team of AI agents to multiply their impact

⚖️ How regulation shapes product development in a highly governed industry — and why that's not a bad thing

🤝 Why the build vs. buy debate has come roaring back, and how smart operators are thinking about their "secret sauce"

James also opens up about what's kept him at Vertafore for eight years — and it speaks volumes about the community they've built.

Whether you're in insurtech, distribution, or just fascinated by how AI is reshaping industries from the inside out, this one is well worth your time.

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What does it take to make AI work in insurance, not just in a pilot, but in production?

In the latest episode of the Leadership in Insurance Podcast, host Alex Bonds sits down with Kyle, founder of Clearcover and the newly launched Dearborn Labs, for a candid conversation about the realities of AI adoption in the insurance industry.

Kyle brings a rare perspective: a decade of building one of insurance's most tech-forward carriers, and now a mission to bring those hard-won lessons to mid-market insurers everywhere. He shares how Clearcover achieved over 90% of claims intake through AI agents and 93% of policies found digitally - and why getting there was far harder than it looked.

In this episode, Kyle and Alex explore:

🔹 Why traditional AI pilots are "a bridge to nowhere" and what truly embedded implementation looks like instead

🔹 The "last mile problem" holding insurers back from real AI value

🔹 How mid-market carriers and MGAs are being underserved by legacy consulting models

🔹 What it takes to embed AI directly into production workflows, not just bolt it on

🔹 The mindset shift required to move from cost centre to P&L impact

With AI capabilities evolving at unprecedented speed, Kyle's message to the industry is unambiguous: "there's no more time to wait." The technology is ready. The hard part is making it fit the business - and that's exactly what Dearborn Labs was built to solve.

Whether you're a carrier, MGA, or insurance leader trying to cut through the AI noise, this episode is essential listening.

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In the latest episode of the Leadership in Insurance Podcast, host Alex Bond sits down with Kasey Roh, Head of US at Upstage AI, for a conversation that stretches from the lessons of large-scale manufacturing automation to the cutting edge of AI-powered document processing in insurance.

Kasey brings a rare perspective — shaped by hyper-growth stints at Meta and Tesla — to the world of enterprise AI.

She reflects on witnessing Tesla's journey to scale Model 3 production, where the hard-won lesson was clear: attempting to automate before truly understanding every step of the process is a costly mistake. Only by mapping workflows end-to-end with domain experts first did the operation find its footing — a principle she carries directly into how Upstage approaches AI adoption in insurance today.

In this episode, Kasey and Alex explore:

🔹 Why understanding end-to-end workflows is non-negotiable before any automation begins

🔹 How Upstage made the leap from the Korean enterprise market — where it now powers over 60–70% of claims processing — to cracking the US market

🔹 The critical difference between how Asian and North American enterprises buy technology

🔹 Why OCR and LLM technology is transforming underwriting and claims processing, handling the complex "tail end" of documents that traditional systems simply can't

🔹 Whether AI will truly disrupt existing carriers, or whether it's the new AI-native players who will reshape the industry first

Kasey also shares her candid take on AI adoption in insurance: the proof-of-concept phase is ending, and organisations that haven't figured out governance and human oversight are going to struggle in the scale-up.

Whether you're in underwriting, claims, or leading digital transformation at a carrier, this episode is packed with hard-won lessons from someone who has scaled technology at some of the world's most demanding and successful companies.

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